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Morning

Start at the Museo Archeologico Mecenate, a museum of corallino pottery and other ancient artifacts that stands on the former amphitheatre.

Head up to Piazza Grande for a cappuccino at one of the cafés under Vasari’s Loggia. Admire the square’s Gothic and Renaissance palazzi before visiting Santa Maria della Pieve.

Climb up past the Casa di Petrarca (the poet’s supposed house) to the Duomo and its masterful stained glass. On Thursday and Friday mornings you could first nip to the tiny Museo del Duomo to see paintings by Bartolomeo della Gatta, and Spinello and Parri Aretino.

Wander back downhill for lunch at La Buca di San Francesco .

Afternoon

Having pre-booked (0575 900 404), head for the Piero works in San Francesco (see Arezzo’s San Francesco).

Grab a heavenly gelato (icecream) from Caffè dei Costanti , and walk down Via Cavour to the Badia. Above the high altar (Vasari’s intended tomb) note the trompel’oeil “dome” (1702) painted by Baroque master of illusion Andrea Pozzo.

Via Garibaldi leads past SS. Annunziata to the Museo Statale d’Arte Medievale e Moderna, a mix of Romanesque sculpture, majolica ceramics, and paintings by Parri Aretino, Bartolomeo della Gatta and Vasari.

Morning

Start with the Duomo group, especially if it’s winter, as the museum closes in the afternoon. Explore the Gothic nooks and Baroque crannies of the cathedral itself first, then pop across to Santa Maria della Scala.

Don’t skip the Museo Metropolitana (see Museo Metropolitana: Duccio’s Maestà) with works by Giovanni Pisano, Donatello and Duccio, plus fabulous views from the unfinished façade wall.

Descend the stairs to see the Baptistry before heading back around the other side of the Duomo for lunch at Antica Osteria da Divo .

Skip dessert so that you can pick it up at Bini pastry shop around the corner at Via dei Fusari 9–13 (don’t eat it just yet).

Afternoon

Stroll down Via di Città, where there are plenty of attractive shops on your way to II Campo (see Piazza del Campo). Either eat your pastries from Bini or grab an outdoor table at Bar II Palio, Piazza del Campo 47–9. Order a coffee or glass of wine, and drink in the ambience of one of the loveliest squares in Italy.

Head inside the Palazzo Pubblico for the Museo Civico displaying Siena’s greatest Gothic art. Exit the Campo on the north side to join the locals for a bracing espresso or Campari at famed café Nannini before continuing up Via Banchi di Sopra as part of the lively evening passeggiata .

Morning

A 9am start in Chiusi, at the Museo Archeologico Etrusco. After learning about the Etruscans, head across the piazza to join a Labirinto di Porsenna tour. They leave every half hour, so you might be able to squeeze in a 10-minute tour of the Museo della Cattedrale as well.

Pick up winding SS146 to Montepulciano . Park at the base of town to stroll up Via Gracciano nel Corso (its name changes constantly), sampling wines along the way. Since 1858, Liberty-style Caffè Poliziano (Via Voltaio nel Corso 27-29), has served light lunches with countryside views.

Afternoon

Continuing up the main street, pop inside the Gesù for Andrea Pozzo’s illusionary painted “dome”. Next, it’s Piazza Grande (more winery shops) and then on to the Duomo.

En route to Pienza at Montepulciano’s edge, turn right (signposted) to see the Tempio di San Biagio (but skip the bare inside). Pienza is a quick stop. After admiring the altarpieces in the Duomo (see Churches Outside Florence) and giant cracks from the cliff’s settlement, tour Pius II’s Palazzo Piccolomini. An alley by the palazzo leads to Via Gozzante, a panoramic walkway out of town.

Go on to Montalcino . If you’re visiting in summer, head to the fortress for sunset views from the ramparts. In winter, make your way to the Caffè Fiaschetteria Italiana in the main square.

Morning

Start with Pistoia and the stupendous Gothic frescoes inside Capella del Tau (incredibly, a private owner in the 16th century whitewashed over them). Go down to zebra-striped San Giovanni Fuoricivitas for a Romanesque feast.

Pop next door into what was once part of the church but now houses the Café Valiani for flaky croissants and cappuccino. Don’t dawdle: you need time for the Duomo (closes at noon, (see Churches Outside Florence)) then Sant’Andrea (closes 12:30). Head back to the centre by way of Ospedale del Ceppo and its terracotta reliefs. Join the locals for a hearty lunch at workaday Lo Storno trattoria just off the picturesque market square where medieval-style second storeys project over the ground floors of the buildings.

Afternoon

From Pistoia, it’s a quick drive to Prato . Stop first at Palazzo Daitini’s frescoes (the St Christopher by the door was a common feature, believed to help protect those leaving the house) to pay your respects to the medieval Merchant of Prato, who inscribed his account ledgers “For God and Profit”.

Do the Duomo (see Churches Outside Florence) and, if you have time, the adjacent Museo del’Opera del Duomo and the Palazzo Pretorio. Grab a bag of cantucci at Antonio Mattei and clamber onto the broken ramparts of Castello dell’Imperatore for a nice view of Santa Maria delle Carceri (1485–1506), a fine High Renaissance church.